40025-25-0Relevant academic research and scientific papers
Method for preparing furan compound from brominated arone
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Page/Page column 7-8, (2021/06/13)
The invention provides a method for synthesizing a furan compound by taking brominated arone and methyl ketone or cyclic ketone as raw materials and directly reacting under the action of tetraisopropyl titanate. The method comprises the following steps: under the protection of inert gas, stirring and heating a reaction mixture of methyl ketone or cyclic ketone and bromo-arone, and then adding tetraisopropyl titanate for reaction; and after the reaction is finished, separating and purifying the obtained reaction mixture to obtain the polysubstituted furan compound. The synthesis method provided by the invention has the advantages of easily available raw materials, low cost, simple operation and easy control, no solvent, good substrate universality and functional group compatibility, and is suitable for industrial mass production.
Divergent Reaction Pathways of β-Chlorovinyl Ketones: Microwave-Assisted Thermal Nazarov Cyclization versus Cycloisomerization via Soft Vinyl Enolization
Kim, Hun Young,Oh, Kyungsoo
supporting information, (2020/02/21)
Divergent reaction pathways of β-chlorovinyl ketones have been established to provide stereodefined alkylidenecyclopent-2-enones and 2-alkenylfuran derivatives. The switch of the reaction pathways was made possible by the microwave-assisted thermal Nazaro
Electrocyclization reactions of 1-Aza- and 1-oxapentadienyl and -heptatrienyl cations: Synthesis of pyrrole and furan derivatives
Alickmann, Dirk,Froehlich, Roland,Maulitz, Andreas H.,Wuerthwein, Ernst-Ulrich
, p. 1523 - 1537 (2007/10/03)
Quantum chemical DFT calculations (B3LYP/6-31+G) have been used to gain insight into the conformational and energy properties of the 1-aza- and 1-oxapentadienyl and -heptatrienyl cations 1, 2, 3, and 4. The calculated thermodynamic and kinetic data of the ring-closure reactions giving the cyclic products 5-14 are reported and discussed with respect to the experimental results. Experimentally, synthetic routes to the α,β-unsaturated carbonyl compounds 24 and 27, each with a leaving group in the γ-position, have been developed. These compounds have been investigated with respect to their ability to undergo 1,5-electrocyclization reactions to yield 2,5-disubstituted furans 28 upon heating in the presence of acid, presumably through the intermediate formation of the 1-oxapentadienyl cations 2. From the corresponding imine 29a the pyrrole 30d was obtained after treatment with tetrakis (triphenylphosphane) palladium. In the presence of benzylamine and the Pd° catalyst, the corresponding pyrroles 30a-c were formed from 24 and 27. The homologous α,β,γ,δ-unsaturated carbonyl compounds 31 afforded 2-vinyl-substituted furans 32 upon heating with acid, and the 2-vinyl-substituted pyrroles 34 on treatment with benzylamine and the Pd catalyst. No seven-membered heterocyclic rings were formed. Surprisingly, the α,β-unsaturated carbonyl compounds with two phenyl substituents at the γ-position also provided pyrrole derivatives 40 through a formal dimerization. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
ARYLATION OF FURAN COMPOUNDS BY ARENEDIAZONIUM SALTS
Obushak, N. D.,Ganushchak, N. I.,Lesyuk, A. I.,Dzikovskaya, L. M.,Kisilitsa, P. P.
, p. 748 - 753 (2007/10/02)
3-(5-Aryl-2-furyl)acrylic acids were obtained by the reaction of 5-arylfurfurals with malonic acid.They were arylated by diazonium salts with decarboxylation and the formation of 5-aryl-2-styrylfurans.The latter were also obtained by the interaction of furylacrolein with diazonium salts.This reaction also gave 3-(5-aryl-2-furyl)acroleins and the corresponding arylfurylacrylic acids, which were arylated again with the release of CO2 and the formation of 5-aryl-2-styrylfurans. 3-(5-Aryl-2-furyl)acroleins were also synthesized by the condensation of 5-arylfurfurals with acetaldehyde under phase-transfer conditions.The s-trans configuration of the furan ring and the exocyclic double bond were established in the obtained compounds by the PMR method.
